Hermann wagnee



Patented July- 25, 1933 r HERMANN' WAGNER, or BAD sonnmon-rrrrn-rannns, AND-{HERBERT KRAcKE OR FRANKFORT ON THEJvIAIN, GERMANY, ASSIGNORS To GENERAL ANILINE woRKs, 11%., on NEW YORK,-1\T: Yea CORPORATION or DELAWARE" a Nnw 1.4-DIAIJKOXY BE ZRNR COMPOUNDS No Drawing. Application filed (some 10, 1936, seat in. 487,898, andin Gamay December 11', 1528,.

The present inventionrelates to the new compounds of the following general formula V j ,alkyl wherein X represents hydrogen, a nitro or an amino group. 7

These compounds are obtainable, for instance, as follows:

A 1-amino-2.5-dialkoXy-benzene may be diazotized and the diazo group exchanged for a chloro group according to the well-known method of Sandmeyer. In this way the 1-chloro-2.5-dialkoxy-benzenes are obtainable. 1

When starting from a 1-amino-2.5-dial koxy-4-nitrobenzene the chloro-2.5-dialkoxy- 4-nitroor -4c-amino-benzenes are obtainable by exchanging in the starting materials the amino group according to Sandmeyer by the chloro group and when preparing the l-amino compounds subjecting the 1-chloro-2.5-dialkoxy-t-nitro-benzenes thus obtainable to a reducing process. The 1-chl0ro-2'.5-dialkoXy-benzenes are in general fluid compounds, possessing a weakly yellowish-green coloration. 1-chloro-2.5-dimethoxybenzene, for instance, boils at 124 C.126 C. under a pressure of 17-l8 mm.

The l chloro-2.5-dialkoxy4-nitrobenzenes are in the dry state solid compounds, possessing a yellow coloration. 1-chloro-2.5-dimethoxyi-nitrobenzene, for instance, forms when recrystallized from alcohol lemon-yellow needles melting at 144 C.1l5 C.

The 1 -chloro-2.5 dialkoxy amino-ben- 7 zones are in thedry state solid compounds.

l-chloro 2.5 dimethoxyl-amino-benzene, for instance, forms when recrystallized from alcohol white needles melting at, 118 G.- 119 C. a r

The following examples illustrate the p invention, but they are not intended to limit it thereto:

(1) 153 grams of 1-amino-2.5-dimethoxybenzene obtainable, for instance, according I sodium nitrite at a temperature of 5 G. I clear diazo solution 1s run into a solution of has separated is filtered by suction.

toiAnmlen'QWQ Pages 258 a d 254, are dis- 5 solved in 300 com. of hydrochloric acid of 20 Be. and 1000 ccm. of water and the whole is diazotized 'by meansflof 71 grams of C. containing. 100 grams of cuprous chloride and'500ccm. of hydrochloric acid of chloro-2.5-dimethoxybenzene thus" formed is The I expelled by means of steam; It forms a feebly yellow oil boiling undera reduced pres sure of'17-18 mm. at a'temperature of from 124 C.l26 C. Y

By using instead" of 1-a1nino-2.5-di

, methoxybenzene other dialkylethers 10f ami- F '5 nohydroquinone, there are obtainable the corresponding chloro-hydroquinonedialkylethers. V 1

(2) 198 gramsof 1amino-L-nitro-25-di-' inethoxybenz'ene obtainable, for instance, ace

cording to DRP. 14:1 975 or according to" I Berichte 17, 2 121 and "DltP. 1 11 398 are stirred with 300 com. of hydrochloric acid of 20 B. and water and the wholeis diazotized while adding ice. The diazo solution which, if necessary, may be filtered by suction is run at a temperature of C.

into a solution of'100 grams of cuprous chloride and 500 com. of hydrochloric acid of 20 B. chloro-el-nitro-2.5-dimethoXy-benzene which It forms when recrystallized from alcohol lemon-yellow needles melting at Mel-145 C.

l-amino-l nitro-2.5-dihydroXy-benzene, there are obtainable according to the process above described the corresponding l-ChlOIO-l-DitlO- 2.5- dialkoXy-benzenes.

When frothing has ceased the 1 By using instead of1-amino-4-nitro-25- dimethoxybenzene other dialkylethers of -(3)"200 grams of l-choloro-4-nitro-25- dimethoXy-benzene obtainable according to Example 2are-reduced at a temperature of from to C. by means of 200grams tion mass is rendered alkaline by means of .9 of iron turnings, 2 liters of water and 25 com. or hydrochloricflacid of 20 B- The reduc sodium carbonate, the ferruginous mud is filtered by suction and dried. The base'thus obtained is extracted by means of alcohol. By evaporating the alcohol, the'base crystallizes in the form of brownish needles, and after being re-dissolved once more from alcohol, the 1-chloro-4-amino-2.5-dimethoxybenzene is obtained in the form ofw'hite needles melting at 118 G'.119 C.

a By using instead of 1-ch1oro-4-nitro-2.5-

dimethoxy-benzene other dialkylethers, thereare obtainable the corresponding amino di-- rivatives.

WVe claim: '1, As new products the compounds of the following general formula wherein X represents hydrogen, a nitro or an ammo group.

F-Oflf: wherein X represents hydrogen or an amino roup. HERMANN WAGNER, HERBERT RAOKER.

1 its 

